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New Thiochromans via Reductive Cyclization of Thiophenol Derivatives

  作者 NIERMANN ANDRE; GROESSEL JANINE E; REISSIG HANSULRICH  
  选自 期刊  SYNLETT;  卷期  2013年-2;  页码  177-180  
  关联知识点  
 

[摘要]Reductive cyclization of sulfur-containing substrates 1 and 5 with samarium diiodide afforded the corresponding thiochroman derivatives with excellent diastereoselectivities. Cyclization of 1 is facilitated by geminal dimethyl substitution, which accelerates the reductive coupling and prevents samarium diiodide induced dehalogenation. Bromo-substituted dihydrothiochroman derivative 8 was further functionalized in subsequent reactions. Analogously, bromo-substituted hexahydroquinoline derivative 10 was diastereoselectively prepared in satisfying yield.

 
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